Plasticized polyvinyl acetal



Patented Aug. 7, 1945 UNITED STATES PATENT FFICE PLASTICIZED POLYVINYL ACETAL La Verne n. Cheyney, Akron, 0hio, assignor to Wlngtoot Corporation, Akron, Ohio, a corporatlon of Delaware No Drawing. Application October 21, 1M2,

Serial N0. 452,819

( C1. zoo-es) 7 Claims.

This invention relates to the use of plasticizers in polyvinyl acetal compositions. Polyvinyl acetals'are formed by the condensation oi an aldehyde with a, partially hydrolyzed polyvinyl ester, such as polyvinyl acetate or polyvinyl .butyrate or polyvinyl propionate, etc.

The plasticizers used according to this invention are amides formed by the condensation of an amine with a higher monocarboxylic fatty acid; that is, a fatty acid which contains at least five carbon atoms besides that in the carbonyl group. Theacid may, for example, contain as many as thirty carbon-atoms. In forming the sen substituted derivatives.

acyl amide,'the acid may be reacted with ammonia, a primary or secondary aliphatic amine, or a poly'alkylene polyamine. The preferred plasticizers are the amides produced from polyallwlene polyamides.

The effect of the plasticizer is illustrated in the following table which compares the properties of certain plasticized films about'.002 inch thick with two diflerent controls. The first;

control is a polyvinyl butyral resin, which contains no plasticizer, and the second control contains dibutyl sebacate as a plasticizer. The

second comparison is given to show the difierences in a polyvinyl acetal Dlasticized with a usual ester plasticizer and the same polyvinyl acetal plasticized with th s plasticizer and con-- taining an acyl amide in addition.

Stress-strain properties of plasttcizedflims Load at- Ultimate (parts fi i msin) 207 1007 'lensil El olong., 01011 strength, tion, kgJcmJ ta/cm! kgJcm. percent None (control fllm).. 310 k 370 a) n-csproamldo 89 87 an amide oi rlc sold and tetrseth pentomine (1 mo 1 mole)- 1m 16! 310 in) 4 an amide of c acid and tetrasth lens pen- 2 mo 1 mole 95 M 210 20 amide of m lc sci triethy tctrsmine (1 molczl mulch" 131 372 21.0 m amide oi stearic and tctraeth lens tunineflmo 1111010). 86 141 282 190 so dimethyl ate-amid.-. 2 9 11B 240 10 dibutyl Iehccate (contool 147 m 238 .mo

in dlbuty lsbocsts +10 n 134 212 162 10 dihut lsbacsto +10 v n-cm atoll-amide.--" K 12 82 176 18) I I) 01010 lmids. 81 136 323 220 I) n-cmyl oleomide 40 122 286 no The acyl amides are quite compatible with the polyvinyl acetals. In general, compatibility is increased by shortening the chainv of the acyl .amide or introducing unsaturated linkages. in

some cases it may be Iound desirable to add a diflerent plasticizer, such as dibutyl sebacate or another compounding material to render the polyvinyl butyral and the plasticizer more compatible.

These plasticizers may be employed in the formulation not only of cast films but of other plastic compositions where flexibility, softness,

resistance to tear, resilience, impact strength,

etc., are desirable. Such compositions might advantageously be matings applied to sheet materials, such as cloth or paper, extruded prodnote or molding compositions.

Films of the thickness indicated may be em pl yed. 1'01 the iabrication of packages or for tashioninz garments, such as raincoats, or other products, such as shower curtains, umbrellas. etc. Coated tabrics or paper in which the coating composition contains a polyvinyl acetai resin plasticized with one of the amides of this inven= tion are especially useful for the fabrication of water-proof materials which may be used for some or the same uses as those indicated for the films and which possess additional strength heeauseotthebackinztowhichthe coatingisap plied. Extruded products may take the form or flexible tubing or of calendered sheet material which is an extremely valuable safety-glass interlayer because of its excellent low temperature properties. Molded roducts of the compositions mended. Testsiortherateoihydroaenlas dit- Iusion of polyvinyl acetals plasticised with these particular amidefa showed the rate to be practicaliy the same as that of an-unpiasticized control mm. l ilms plasticized with corresponding amounts 01' normal ester plasticizers, such as dibutyi phthalate and dibutyi sebacate, live as diii'usion rates considerably hilher than that the unplasticimd control film.

What I claim is: 4 e

1. A poivvinyl aoetal composition .piasticized with an amide formed by equal molar proportions oi a poiyaikylene polyamine and a monocarboxylic fatty acid, said acid containing about flve to about thirty carbon atoms.

2. A polyvinyl butyral composition plasticiaed with the amideoi equal molar proportions oi tetraethylene pentamine and a monocarboxylic fatty acid, said'acid containing about 5 to about 30 carbon atoms.

3.- A polyvinyl butyrai composition plasticised with an amide iormed 0! equal molar proportions of tetraethvlene pentamine and lauric acid.

as sheet material coated with a polsvimu v aoetal composition which is plasticilod with an amide formed oi equal molar proportions of a polyalblene polyamine and -a lie iatty acid, said acidicontainin's from 5 to about carbon atoms.

5. A sheet material coated with a polyvinyl butyral composition plasticised with the amide of equal molar proportions oi tetraethyiene Dent-. amine and a monocarboxylic iatty acid, said acid.

containing from 5 toabout carbon atoms.

6. A sheet material coated with. a polyvinyl butyrai composition plasticised with the amide oi equal molar proportions ot tetraethylene pentamine and lauric acid.

7. A sheet material coated'witha i i butyi'ai composition'fplasticized with thede of equal molar proportionsoi apolyalkylene po y-s,

amine and a monocarhoxylic fatty acid. said acid containing from about 5 to about 80 carbon atoms. LA E. CHEYNEY.

CERTIFI GATE OF CORRECTI 0N Patent No. 2, 80,92

August 7, 1915.

LA VERNE E. CHEYNEY.

It is hereby certified that error appears in the printed specification of the above mlmbered patent requiring correction as follows: Page 1, first column, line 18, for "polyamides" read polys'mines--; and that, the said Letters Patent should be reed with this correction therein that the same may conform to the recordbf the case in the Patent Office.

Signed seaied this. 15th day of November, A. D. 1915.

(Seall Leslie Frazer First Assistant Commissioner of Patents.

mended. Testsiortherateoihydroaenlas dit- Iusion of polyvinyl acetals plasticised with these particular amidefa showed the rate to be practicaliy the same as that of an-unpiasticized control mm. l ilms plasticized with corresponding amounts 01' normal ester plasticizers, such as dibutyi phthalate and dibutyi sebacate, live as diii'usion rates considerably hilher than that the unplasticimd control film.

What I claim is: 4 e

1. A poivvinyl aoetal composition .piasticized with an amide formed by equal molar proportions oi a poiyaikylene polyamine and a monocarboxylic fatty acid, said acid containing about flve to about thirty carbon atoms.

2. A polyvinyl butyral composition plasticiaed with the amideoi equal molar proportions oi tetraethylene pentamine and a monocarboxylic fatty acid, said'acid containing about 5 to about 30 carbon atoms.

3.- A polyvinyl butyrai composition plasticised with an amide iormed 0! equal molar proportions of tetraethvlene pentamine and lauric acid.

as sheet material coated with a polsvimu v aoetal composition which is plasticilod with an amide formed oi equal molar proportions of a polyalblene polyamine and -a lie iatty acid, said acidicontainin's from 5 to about carbon atoms.

5. A sheet material coated with a polyvinyl butyral composition plasticised with the amide of equal molar proportions oi tetraethyiene Dent-. amine and a monocarboxylic iatty acid, said acid.

containing from 5 toabout carbon atoms.

6. A sheet material coated with. a polyvinyl butyrai composition plasticised with the amide oi equal molar proportions ot tetraethylene pentamine and lauric acid.

7. A sheet material coated'witha i i butyi'ai composition'fplasticized with thede of equal molar proportionsoi apolyalkylene po y-s,

amine and a monocarhoxylic fatty acid. said acid containing from about 5 to about 80 carbon atoms. LA E. CHEYNEY.

CERTIFI GATE OF CORRECTI 0N Patent No. 2, 80,92

August 7, 1915.

LA VERNE E. CHEYNEY.

It is hereby certified that error appears in the printed specification of the above mlmbered patent requiring correction as follows: Page 1, first column, line 18, for "polyamides" read polys'mines--; and that, the said Letters Patent should be reed with this correction therein that the same may conform to the recordbf the case in the Patent Office.

Signed seaied this. 15th day of November, A. D. 1915.

(Seall Leslie Frazer First Assistant Commissioner of Patents. 

